Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Methyl 7-bromo-4-hydroxyisoquinoline-3-carboxylate | HCID 89813103 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89812927 | HCID 89812927 | — |
Reaction Steps
A mixture of 7-bromo-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester (141.0 mg, 0.50 mmol), xantphos (28.9 mg, 0.05 mmol, Strem), Pd2(dba)3 (22.9 mg, 0.03 mmol, Sigma-Aldrich), Cs2CO3 (488.7 mg, 1.5 mmol) and aniline (0.1 mL, 1 mmol) in DMF (5 mL) was stirred at 135° C. for 16 hours under a nitrogen atmosphere. After cooling to room temperature, the mixture was diluted with CH2Cl2 (50 mL) and H2O (50 mL). The layers were separated and the aqueous layer was extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% MeOH/CH2Cl2) to give the title compound in 62.4 mg. MS: (−) m/z 293.04 (M−1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09409892B2 |
|---|
| Source dataset | uspto-grants-2016_08 |
|---|
| ORD ID | ord-c3afb1eb8d914a5693ac870522a2f2c6 |
|---|
| Source note | uspto-grants-2016_08 |
|---|
